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Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid, Part VI [1]. Synthesis and X-ray structure of model indolo[3,2-b]- and [2,3-b]pyrido[2,3-f]quinoxaline-3-carboxylic esters

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Abstract

Cyclocondensation reaction of ethyl 7,8-diamino-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate with 1-methylisatin produced a separable mixture of the corresponding indolo[3,2-b]- and [2,3-b]pyrido[2,3-f]quinoxaline-3-carboxylates, of which the latter isomer predominates. On the other hand, interaction with 1H-isatin or 5-chloroisatin gave the respective indolo[2,3-b]pyrido[2,3-f]quinoxaline-3-carboxylates as the sole regiospecific products. The structures of these new pentacyclic derivatives are based on microanalytical, spectral (IR, MS, and NMR) and X-ray crystal structure data.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Jordan, Amman, Jordan

    Esráa S. Abu-Sheaib, Jalal A. Zahra & Mustafa M. El-Abadelah

  2. Institut für Anorganische Chemie, Universität Duisburg-Essen, Campus Essen, Essen, Germany

    Roland Boese

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  1. Esráa S. Abu-Sheaib
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  2. Jalal A. Zahra
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  3. Mustafa M. El-Abadelah
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  4. Roland Boese
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Corresponding authors

Correspondence to Jalal A. Zahra or Roland Boese.

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Correspondence: Jalal A. Zahra, Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan; Roland Boese, Institut für Anorganische Chemie, Universität Duisburg-Essen, Campus Essen, Universität strasse 3–5, D-45117 Essen, Germany.

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Abu-Sheaib, E., Zahra, J., El-Abadelah, M. et al. Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid, Part VI [1]. Synthesis and X-ray structure of model indolo[3,2-b]- and [2,3-b]pyrido[2,3-f]quinoxaline-3-carboxylic esters. Monatsh Chem 139, 1061–1066 (2008). https://doi.org/10.1007/s00706-008-0883-7

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